Ethanol → Ethyl (3R)-5-oxo4-(phenylmethyl)-3-morpholinecarboxylate

HRID 2074837Notes

Reaction equation

HRID 2074837 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:6]([C:15]([OH:17])=[O:16])[CH2:5][O:4][CH2:3]1.S(Cl)(Cl)=O.[CH3:22][CH2:23]O>>[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:6]([C:15]([O:17][CH2:22][CH3:23])=[O:16])[CH2:5][O:4][CH2:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl Chloride5×HCID 13543371(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

Product 1

HCID 13543380Ethyl (3R)-5-oxo4-(phenylmethyl)-3-morpholinecarboxylate

Procedure

The title compound was prepared according to the procedure described by H. H. Otto, Helvetica Chimica Acta, 2004, 87, 90 using (3R)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (D44, 3.13 g, 13.33 mmol) in EtOH (30 mL), cooling in an ice bath before adding Thionyl Chloride (1.46 mL) dropwise, and then stirring at R.T. for 6 hours. Added more thionyl chloride (1 mL) and stirring at R.T. overnight. Added more thionyl chloride (1 mL) and stirred for 4 hours, added further thionyl chloride (0.5 mL) and stirred overnight again. Added thionyl chloride (0.2 mL) and left stirring for 5 hours. Solvent evaporated to afford the title compound as an orange oil in quantitative yield.

Workup

  1. customThe title compound was prepared
  2. stirringstirring at R.T. overnight
  3. stirringstirred for 4 hours
  4. stirringstirred overnight again
  5. stirringstirring for 5 hours
  6. customSolvent evaporated

Sources & evidence

ORD record
ord-1fdca6dc479346edbb8595049f16faa4
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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